Senior Director, Revenue Strategy & Operations

Our mission: to eliminate every barrier to mental health.

At Spring Health, we’re on a mission to revolutionize mental healthcare by removing every barrier that prevents people from getting the help they need, when they need it. Our clinically validated technology, Precision Mental Healthcare, empowers us to deliver the right care at the right time—whether it’s therapy, coaching, medication, or beyond—tailored to each individual’s needs.

We proudly partner with over 450 companies, from startups to multinational Fortune 500 corporations, as a leading provider of mental health service, providing care for 10 million people. Our clients include brands you use and know like Microsoft, Target, and Delta Airlines, all of whom trust us to deliver best-in-class outcomes for their employees globally. With our innovative platform, we’ve been able to generate a net positive ROI for employers and we are the only company in our category to earn external validation of net savings for customers.

We have raised capital from prominent investors including Generation Investment, Kinnevik, Tiger Global, Northzone, RRE Ventures, and many more. Thanks to their partnership and our latest Series E Funding, our current valuation has reached $3.3 billion. We’re just getting started—join us on our journey to make mental healthcare accessible to everyone, everywhere.

Reporting to the Vice President of Revenue Operations and sitting on the Revenue Operations leadership team, the Senior Director of Revenue Strategy & Operations is the strategic and operational engine of our go-to-market organization. This individual will own annual and long-range planning, variable compensation strategy and execution, and a team of Field Operations leaders who are deeply embedded with our segment leaders across the business. What makes this role distinct is its mandate as the AI orchestration layer of our AI-native RevOps organization - this leader will architect how people, processes, data, and AI agents work together to drive productivity at scale. This is a full time, remote position on our team. Quarterly travel is required for team/company events or meetings. 

• Lead annual and long-range planning (LRP) end-to-end — from capacity modeling and quota design to territory architecture and headcount alignment — translating company growth targets into executable GTM plans.
• Drive rigorous forecast cadence and scenario planning, partnering with Finance, Sales, and Customer Success leadership to deliver predictable revenue outcomes and clear business visibility to the executive team.
• Architect and own a portfolio of strategic projects and cross-functional initiatives, acting as a trusted operator and thought partner to the CRO and revenue leadership team.
• Own and execute the Revenue operating cadence and rhythm across forecasting, pipeline, strategic deal reviews, and more 
• Own the end-to-end variable compensation strategy, design, and execution across the revenue organization — including plan design, modeling, and administration — ensuring incentive structures are competitive, aligned to business outcomes, and clearly understood by the field.
• Partner with Finance, People, and Sales leadership to model compensation scenarios, run pay equity analyses, and evolve comp plans in response to market and business changes.
• Lead and develop a team of Field Operations partners embedded with segment leaders across the business — evolving their role from operational executors to AI-enabled strategic builders who develop analytics, dashboards, and AI agents in the field, while also being strong strategic and operational partners to our leaders across sales, CS, and partnerships. 
• Ensure Field Operations leaders serve as full-stack partners to their segments: owning business reviews, pipeline hygiene, performance insights, and the build-out of Looker dashboards and AI-powered workflows that accelerate their segments' productivity.
• Serve as the AI orchestration layer for Revenue Operations — defining how AI is adopted within the various segments and how the team deploys AI agents, automation, and analytics tools (including Claude and Looker) across people, process, and data to compound team productivity and decision-making velocity.
• Scale an AI-native operating model for our field teams: establishing standards for prompt engineering, agent deployment, and tool integration; measuring and improving AI productivity gains through; writing end user requirements for underlying data sources and semantic layers as well as for agentic workflows 
• Champion a culture of continuous experimentation and tooling adoption, identifying where AI can eliminate repetitive work, surface insights faster, and enable the team to operate at a level beyond headcount - this means you and your teams are experimenting daily

What success looks like: 

• Planning quality and timeliness: Annual plan and LRP delivered on schedule, with quota attainment rates and ramp-to-productivity metrics tracking at or above industry benchmarks across all segments. Quotas and compensation plans in hand at the start of the fiscal year. 
• Variable compensation accuracy and satisfaction: Compensation plans are administered accurately (< 1% dispute rate), delivered on time, and score favorably on field satisfaction surveys.
• Revenue forecast accuracy: Segment and company-level forecasts fall within ±5% of actuals on a rolling 90-day basis, reflecting strong operational rigor across the Field Operations team.
• AI productivity impact: Measurable and documented productivity gains from AI and analytics deployments across the team — including time savings, faster insight delivery, and reduced manual reporting burden — tracked and reported quarterly.
• Field Operations effectiveness: Business review scores, segment NPS for RevOps partnership, and the volume of self-serve analytics and AI tools deployed in the field improve year-over-year.
• Team development: Field Operations leaders demonstrate measurable growth in analytics and AI capabilities, with clear evidence of skill progression and retention.

What you’ll bring: 

• 12+ years of experience in Revenue Operations, Sales Strategy, Business Operations, Consulting, or a related function at a high-growth B2B SaaS or technology company.
• 5+ years of people management experience, with a track record of developing high-performing teams and evolving team capabilities in response to changing business needs.
• Deep expertise in GTM planning, including annual planning, quota design, territory modeling, headcount planning, and long-range strategic planning.
• Hands-on experience designing and administering variable compensation programs — including plan architecture, commission modeling, payout accuracy, and field communication.
• Strong analytics fluency, including proficiency with Looker (or equivalent BI tools such as Tableau or Sigma) for building dashboards, data models, and self-serve reporting infrastructure.
• Advanced SQL skills or experience working alongside analytics engineering teams to define and validate data models.
• 2+ years of demonstrable experience designing and deploying automation, AI, and/or ML systems in a GTM context (prospecting, forecasting, coaching, data enrichment - to automate workflows, accelerate analysis, and build productivity into operational processes 
• Proven ability to lead cross-functional strategic initiatives with executive-level stakeholders and to distill complex data into clear, actionable recommendations.
• Experience as an operational partner to segment or business unit leaders, translating business performance data into strategic recommendations and enabling field execution.

Nice to have: 

• Experience in healthcare technology, mental health, or mission-driven SaaS environments.
• Hands-on experience with AI agent design, prompt engineering, or deploying AI workflows using tools like Claude (API), Anthropic Console, or similar platforms.
• Familiarity with Salesforce (SFDC) CRM administration, data hygiene practices, and pipeline management workflows.
• Experience building or managing incentive compensation management (ICM) platforms such as Xactly, CaptivateIQ, or Spiff.
• A software engineering mindset: rigorous about testing, observability, data hygiene, and iteration cycles.
• Background in management consulting, FP&A, or corporate strategy — particularly in organizations that have undergone significant GTM transformation.

The target base salary range for this position is $188,000 -  216,000, and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, location, internal pay equity, and other relevant business considerations. We review all employee pay and compensation programs annually using Radford Global Compensation Database at minimum to ensure competitive and fair pay. 

Benefits provided by Spring Health:

Note: We have even more benefits than listed here and below, your recruiter will provide more in-depth information as you continue in the interview process. Benefits are subject to individual plan requirements and eligibility criteria.

• Health, Dental, Vision benefits start on your first day at Spring. You and your dependents also receive access to One Medical accounts HSA and FSA plans are also available, with Spring contributing up to $1K for HSAs, depending on your plan type.
• Employer sponsored 401(k) match of up to 2% for retirement planning
• A yearly allotment of no cost visits to the Spring Health network of therapists, coaches, and medication management providers for you and your dependents.
• We offer competitive paid time off policies including vacation, sick leave and company holidays.
• At 6 months tenure with Spring, we offer parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents.
• Access to Noom, a weight management program—based in psychology, that’s tailored to your unique needs and goals. 
• Access to fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses.
• Access to Wellhub,  which connects employees to the best options for fitness, mindfulness, nutrition, and sleep in one subscription
• Access to BrightHorizons, which provides sponsored child care, back-up care, and elder care
• Up to $1,000 Professional Development Reimbursement a year.
• $200 per year donation matching to support your favorite causes.

Not sure if you meet every requirement? Research shows that women and people from historically underrepresented communities often hesitate to apply for roles unless they meet every qualification compared to other similarly-qualified candidates. At Spring Health, we are committed to fostering a workplace where everyone feels valued, empowered, and supported to Thrive. If this role excites you, we encourage you to apply.

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Spring Health is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic. We also consider qualified applicants regardless of criminal histories, consistent with applicable legal requirements. Spring Health is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans. If you have a disability or special need that requires accommodation, please let us know.